1403230-69-2

Upstream product

• 109425-49-2 Fmoc-Val-Pro-OH 
• 1403230-63-6 Fmoc-Val-Pro-NH-(CH₂)2-NH-Boc 
• 1403230-64-7 C₂₇H₃₄N₄O₄*ClH 
• 1403230-68-1 3-[3'-O-(tert-butyldimethylsilyl)-2'-deoxy-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one 
• 1403230-67-0 3-[3’,5’-di-O-(tert-butyldimethylsilyl)-2’-deoxy-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one 

Downstream Products

• 1403230-61-4 3-[2’-deoxy-5’-O-[2-(valylprolylamino)ethylcarbamoyl]-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one 

Relevant academic research and scientific papers

Dipeptidyl Peptidase IV-Activated Prodrugs of Anti-Varicella Zoster Virus Bicyclic Nucleoside Analogues Containing Different Self-Cleavage Spacer Systems

A new type of double prodrug of the antiviral family of bicyclic nucleoside analogues (BCNA) bearing cyclization self-cleavage spacers between the Val-Pro dipeptide sequence as well as the parent compound were synthesized and evaluated with regard to activation by the DPPIV/CD26 enzyme and for their stability in human and bovine serum. In buffer solution, carbamate and ester prodrugs were found to be chemically stable. Most prodrugs containing a dipeptidyl linker efficiently converted into the BCNA parent drug. In contrast, the Val-Pro alkyldiamino prodrugs converted predominantly into their alkyldiamino prodrug intermediates in the presence of CD26 and human serum. A marked increase in water solubility was observed for all prodrugs. In contrast to the parent compound, a tetrapeptide prodrug containing the Val-Val dipeptide as a self-cleavage spacer released substantial amounts of the BCNA parent drug at the basolateral side of Caco-2 cell cultures and exhibited 15- to 20-fold increased bioavailability in mice relative to the poorly bioavailable parent compound.